Lithium borohydride → (2R,4R)-tert-Butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 908449Notes

Reaction equation

[BH4-].[Li+].[C:3]([Si:7]([CH3:26])([CH3:25])[O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:11]([C:21](OC)=[O:22])[CH2:10]1)([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([Si:7]([CH3:26])([CH3:25])[O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[C@@H:11]([CH2:21][OH:22])[CH2:10]1)([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 20 °C

Procedure

2M Lithium borohydride in THF (15.06 ml) was added slowly to a stirred solution of O1-tert-butyl O2-methyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxypyrrolidine-1,2-dicarboxylate (10.35 g) in THF (100 ml) at 0° C. The resulting mixture was allowed to warm to 20° C. and stirred for a further 18 hours. The reaction mixture was quenched with water and evaporated to remove THF. The aqueous residues were extracted with DCM (250 ml). The organic phase was washed sequentially with water (250 ml) and saturated brine (250 ml), dried over Magnesium sulphate, filtered and evaporated to give tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (9.32 g). NMR Spectrum: (DMSOd6) 0.01 (6H, s); 0.80-0.82 (9H, m); 1.34 (9H, s); 1.84-1.89 (1H, m); 1.99 (1H, m); 3.00 (1H, m); 3.53-3.57 (4H, m); 4.28 (1H, s); 4.48-4.49 (1H, m).

Workup

customThe reaction mixture was quenched with water
customevaporated
customto remove THF
extractionThe aqueous residues were extracted with DCM (250 ml)
washThe organic phase was washed sequentially with water (250 ml) and saturated brine (250 ml)
dry with materialdried over Magnesium sulphate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-0b7e572a059b4607bec4b55817d730b8
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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