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Water → HCID 10883437, compound

HRID 1422067
Notes
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Reaction equation

HRID 1422067 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:30][CH3:31])=[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[N:18]3[C:19]=2[CH:20]=[C:21]4[C:26](OC)=[O:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3=[CH:20][C:21]([CH2:26][OH:27])=[C:22]4[N:18]3[C:17](=[CH:25][CH:24]=[CH:23]4)[C:16]=2[CH2:30][CH3:31])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11144022HCID 11144022, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10883437HCID 10883437, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylate (8.5 g, 20.8 mmol) was dissolved in 170 ml of dry tetrahydrofurane under a nitrogen atmosphere. Lithium aluminium hydride (1.24 g, 32.6 mmol) was added in portions and stirring was continued for 21/2 hours. Water (10 ml) was added dropwise, and 95 ml of saturated aqueous potassium carbonate and 200 ml of diethyl ether was added. The organic layer was separated, and the aqueous layer was extracted with diethyl ether (2×300 ml). The combined organic layers were washed with 200 ml of water and dried over sodium hydrogen carbonate. The solvent was evaporated and the remaining product was dried to afford 7.7 g (97%) of the title compound as yellow crystals. M.p. 148-150° C. MS(SP): m/z 381 (M+). 1H-NMR (CDCl3, 300 MHz) δ: 1.48 (t, 3H); 3.23 (q, 2H); 5,17 (s, 2H); 5.18 (s, 2H); 7.14 (d, 2H); 7.32-7.52 (m, 5H); 7.57 (s, 1H); 7.65 (t, 1H); 7.72 (d, 2H); 7.92 (d, 1H); 8.02 (d, 1H).

Workup

  1. custom2 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethyl ether (2×300 ml)
  4. washThe combined organic layers were washed with 200 ml of water
  5. dry with materialdried over sodium hydrogen carbonate
  6. customThe solvent was evaporated
  7. customthe remaining product was dried

Sources & evidence

ORD record
ord-2f1153f346d741378f5230c22571cf97
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06080754

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes