Cyclopropylamine → HCID 86751658, compound

HRID 2294733Notes

Reaction equation

HRID 2294733 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH:13]3[CH2:15][O:14]3)[O:11][C:10]([CH3:17])([CH3:16])[N:9]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>CO>[CH:1]1([CH2:7][C@H:8]2[C@H:12]([C@@H:13]([OH:14])[CH2:15][NH:28][CH:25]3[CH2:27][CH2:26]3)[O:11][C:10]([CH3:17])([CH3:16])[N:9]2[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 53704761HCID 53704761, compound

Product 1

HCID 86751658HCID 86751658, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 733 mg (2.16 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-5-[(RS)-2-oxiranyl]-3-oxazolidinecarboxylate (WO 88/4664) and 2 ml of cyclopropylamine in 15 ml of methanol is stirred at 50° overnight under argon. Thereafter, the reaction mixture is evaporated and, for purification and separation of the epimers, the residue is chromatographed on 100 g of silica gel using a 98:2 mixture of chloroform and methanol as the eluent. There are obtained 185 mg of the less polar tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-2-(cyclopropylamino)-1-hydroxyethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, MS: 397 (M+H)+, and 341 mg of the more polar tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(R)-2-(cyclopropylamino)-1-hydroxyethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, MS: 397 (M+H)+, each as a colourless oil.

Workup

  1. customThereafter, the reaction mixture is evaporated and, for purification and separation of the epimers
  2. customthe residue is chromatographed on 100 g of silica gel using
  3. additiona 98:2 mixture of chloroform and methanol as the eluent

Sources & evidence

ORD record
ord-b49997dfbdff42d1a4d63faf81caae32
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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