Methanol → Benzyl (s)-1-((1s,2r,4r/s)-4-(tert-butylamino)-2-propylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 1171527Notes

Reaction equation

[O:1]=[C:2]1[C@@H:6]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4][N:3]1[C@H:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][C@H:19]1[CH2:25][CH2:26][CH3:27].[C:28]([NH2:32])([CH3:31])([CH3:30])[CH3:29].CO.[BH4-].[Na+]>C(Cl)Cl.[OH-].[Na+].CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[C:28]([NH:32][CH:21]1[CH2:22][CH2:23][C@H:18]([N:3]2[CH2:4][CH2:5][C@H:6]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:2]2=[O:1])[C@H:19]([CH2:25][CH2:26][CH3:27])[CH2:20]1)([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A sample of benzyl (S)-2-oxo-1-((1S,2R)-4-oxo-2-propylcyclohexyl)pyrrolidin-3-ylcarbamate (114 mg) was dissolved in Ti(OiPr)4 (1.5 mL, 5.0 mmol) and tert-butylamine (0.14 mL, 1.8 mmol). The resultant solution was stirred at RT for 3 h before being cooled to 0° C. and charged successively with MeOH (2 mL) and NaBH4 (22.8 mg, 0.6 mmol). The mixture was stirred for 90 min while the solution slowly warmed to RT. The solution was diluted with methylene chloride (10 mL) and 0.5 N NaOH was added. The resultant suspension was filtered through a pad of Celite with EtOAc washings and the filtrate was dried, filtered, and concentrated in vacuo to afford benzyl (S)-1-((1S,2R,4R/S)-4-(tert-butylamino)-2-propylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate as an inseparable mixture of diastereomers. MS found: (M+H)+=430.5.

Workup

temperatureslowly warmed to RT
additionwas added
filtrationThe resultant suspension was filtered through a pad of Celite with EtOAc washings
customthe filtrate was dried
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-11c9bceb83b642e9b44720682e86e2ef
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829571B2

Reaction notes

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