Triethylamine → HCID 69435132, compound

HRID 1006781Notes

Reaction equation

HRID 1006781 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][S:8][C@H:9]2[CH2:13][NH:12][C@H:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10]2)=[CH:5][CH:4]=1.C(N([CH2:25][CH3:26])CC)C.[CH2:27]([O:31][C:32](Cl)=[O:33])[CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[CH2:27]([O:31][C:32]([N:12]1[CH2:13][C@H:9]([S:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=2)[CH2:10][C@H:11]1[CH2:14][CH2:15][CH2:16][O:17][C:32]([O:31][CH2:27][CH2:28][CH2:25][CH3:26])=[O:33])=[O:33])[CH2:28][CH2:29][CH3:30].[CH2:27]([O:31][C:32]([N:12]1[CH2:13][C@H:9]([S:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=2)[CH2:10][C@H:11]1[CH2:14][CH2:15][CH2:16][OH:17])=[O:33])[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 69434676HCID 69434676, compound

Product 2

HCID 69428442HCID 69428442, compoundYield 28%HCID 69435132HCID 69435132, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 615 mg (2.19 mmol) (2R,4R)-3-[4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-yl]-propan-1-ol and 0.34 ml (2.40 mmol) triethylamine in 5 ml CH2Cl2 was cooled to −10° C. and treated slowly with 0.31 ml (2.29 mmol) butylchloroformate. After 20 min at this temperature the reaction was extracted with cold (0° C.) aqueous 10% KHSO4/Et2O (3×). The organic phase was washed with aqueous saturated NaHCO3 dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with hexane/EtOAc (2:1 to 1:1) gave 340 mg (32%) of (2R,4R)-2-(3-butoxycarbonyloxy-propyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester and 230 mg (28%) of (2R,4R)-2-(3-hydroxy-propyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester, MS: 382 (MH+).

Workup

  1. extractionAfter 20 min at this temperature the reaction was extracted with cold (0° C.) aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phase was washed with aqueous saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-0abb5767f75947a58e14f5e8aaea000c
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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