Triethylamine → (RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester

HRID 602804Notes

Reaction equation

HRID 602804 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])([CH:6]1[CH2:18][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)[CH3:5].C(N(CC)CC)C.[O:36](C(OC(C)(C)C)=O)[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:40]([O:39][C:37]([N:10]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][C:16]=2[C:8]2[CH2:7][CH:6]([C:4]([S:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)(=[O:21])=[O:20])([C:3]([O:2][CH3:1])=[O:28])[CH3:5])[CH2:18][C:9]1=2)=[O:36])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 11430019(RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester

Product 1

HCID 67266834(RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl esterYield 94.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

130 mg (0.31 mmol) (RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester were dissolved in 7 mL CH2Cl2 at RT. 90 μL (0.62 mmol, 2 eq) triethylamine, 4 mg (0.031 mmol, 0.1 eq) DMAP and 81 mg (0.37 mmol, 1.2 eq) BOC2O were added. The reaction mixture was stirred for 2 hours. The reaction was quenched with 10 mL of an aqueous 1M solution of HCl. The organic layer was separated and the aquous layer was washed with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and evaporated to dryness to yield to 152 mg (94%) (RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester as a white powder, M: 535 (MNH4+).

Workup

  1. customThe reaction was quenched with 10 mL of an aqueous 1M solution of HCl
  2. customThe organic layer was separated
  3. washthe aquous layer was washed with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b5e7f900249445efa9a4b9212628d74e
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

Loading…