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Diethyl Ether → Methyl 3-Benzyl-1,2,3,3a,4,5-hexahydro-4-(2,2-dimethyl-3-hydroxypropyl)-7H-pyrrolo (2,3-d) carbazole-6-carboxylate

HRID 1905076
Notes
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Reaction equation

HRID 1905076 reaction equation
[CH2:1]([N:8]1[CH:12]2[CH:13]([CH2:28][C:29]([CH3:40])([CH3:39])[CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH2:14][C:15]([C:24]([O:26][CH3:27])=[O:25])=[C:16]3[NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:11]23[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].C(OCC)C>C1COCC1.O>[CH2:1]([N:8]1[CH:12]2[CH:13]([CH2:28][C:29]([CH3:40])([CH3:39])[CH2:30][OH:31])[CH2:14][C:15]([C:24]([O:26][CH3:27])=[O:25])=[C:16]3[NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:11]23[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 14750128methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-[2,2-dimethyl-3-(t-butyldimethylsilyloxy)propyl]-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

Product 1

HCID 14750129Methyl 3-Benzyl-1,2,3,3a,4,5-hexahydro-4-(2,2-dimethyl-3-hydroxypropyl)-7H-pyrrolo (2,3-d) carbazole-6-carboxylate
Yield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 873 mg (1.56 mmol) of methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-[2,2-dimethyl-3-(t-butyldimethylsilyloxy)propyl]-7H-pyrrolo(2,3-d)carbazole-6-carboxylate in 30.5 mL of THF and 15 mL of water was added 5.24 g (20 eq) of p-toluenesulfonic acid. The reaction mixture was stirred for 90 min. at 20° C. and saturated aqueous K2CO3 solution was added until a pH=9-10 was obtained. Ethyl ether (100 mL) was added and the two layers were separated. The aqueous layer was extracted once with 100 mL of ethyl ether and twice with 100 mL of CH2Cl2. The combined organic layers were dried over MgSO4 and the solvents evaporated in vacuo (aspirator). The crude product was purified by column chromatography on silica gel (40 g). Elution with CH2Cl2 followed by ethyl ether gave 0.678 g (97.5%) of the title compound as a white foam. TLC: (Silica) Rf 0.50 (ethyl ether), detection with CAS (blue with developing yellow center), UV (long and short wave length).

Workup

  1. customwas obtained
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted once with 100 mL of ethyl ether and twice with 100 mL of CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvents evaporated in vacuo (aspirator)
  6. customThe crude product was purified by column chromatography on silica gel (40 g)
  7. washElution with CH2Cl2

Sources & evidence

ORD record
ord-05d2852d45d84700b088370e01c7afaa
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04841045

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes