Water → HCID 86589643, compound

HRID 1006339Notes

Reaction equation

HRID 1006339 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@@H:13]1[CH2:41][N:16]2[C@H:17]([CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][C@@H:15]2[CH2:14]1.C(N(CC)CC)C.O>ClCCl>[CH:28]([C@H:17]1[N:16]2[CH2:41][C@@H:13]([NH:12][C:2]([O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:3])[CH2:14][C@H:15]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86589644HCID 86589644, compound

Product 1

HCID 86589643HCID 86589643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (58 μl) in dichloromethane (0.5 ml) was added dropwise to an ice-cooled solution of tert-butyl (4R,7S,8aS)-7-amino-4-benzhydrylhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate and triethylamine (96 μl) in dichloromethane (2 ml), and the whole was stirred for 2 hours at the same temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure. The syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1). The fractions containing the objective compound were collected to give tert-butyl (4R,7S,8aS)-4-benzhydryl-7-[(benzyloxycarbonyl)amino]hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (190 mg) as a syrup.

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1)
  6. additionThe fractions containing the objective compound
  7. customwere collected

Sources & evidence

ORD record
ord-a7c2f05e68e74008b838ce996fef959d
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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