Water → tert-butyl (2R,4S)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1443004Notes

Reaction equation

HRID 1443004 reaction equation
[BH4-].[Li+].[Si:3]([O:10][C@@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:13]([C:23](OC)=[O:24])[CH2:12]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].C(=O)([O-])O.[K+].O>CCOCC>[Si:3]([O:10][C@@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:13]([CH2:23][OH:24])[CH2:12]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 4148881Lithium borohydrideHCID 866078061-(Tert-butyl) 2-methyl (2R,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 66962096tert-butyl (2R,4S)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium borohydride (2M solution in THF, 6.19 ml) was added dropwise to a stirred solution of 1-tert-butyl 2-methyl (2R,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate (891 mg) in ether (100 ml) at 0° C. under an atmosphere of nitrogen. The mixture was allowed to warm to room temperature and stirred for 3 hours. A saturated solution of potassium hydrogencarbonate (5 ml) was added slowly, followed by water (20 ml). The ether layer was separated, and the aqueous layer washed with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give tert-butyl (2R,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)pyrrolidine-1-carboxylate as a clear oil (750 mg, 88%), which was used without further purification; NMR spectrum (CDCl3) 4.82 (d, 1H), 4.26-4.28 (m, 1H), 4.13-4.15 (m, 1H), 3.67-3.73 (m, 1H), 3.55 (ddd, 1H), 3.42-3.46 (m, 1H), 3.35 (dd, 1H), 1.92-2.01 (m, 1H), 1.48 (s, 9H), 0.91-0.97 (m, 1H), 0.88 (s, 9H), 0.07 (s, 6M).

Workup

  1. customThe ether layer was separated
  2. washthe aqueous layer washed with DCM (3×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d651246e3bc435fa6ebe63c9b6cd8af
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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