Water → (2R,4R)-tert-butyl 4-(benzyloxymethoxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 869657Notes

Reaction equation

HRID 869657 reaction equation
[CH2:1]([O:8][CH2:9][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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].[BH4-].[Na+].O>C(O)C>[CH2:1]([O:8][CH2:9][O:10][C@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@@H:13]([CH2:23][OH:24])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 66960641(2R,4R)-1-tert-butyl 2-methyl 4-(benzyloxymethoxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 66961725(2R,4R)-tert-butyl 4-(benzyloxymethoxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (2R,4R)-1-tert-butyl 2-methyl 4-(benzyloxymethoxy)pyrrolidine-1,2-dicarboxylate (2.29 g, 6.27 mmol, EXAMPLE 79 Step 1) and lithium chloride (586 mg, 13.8 mmol) in ethanol (25 mL) was added sodium borohydride (522 mg, 13.8 mmol) at 0° C., and the mixture was stirred at room temperature for 24 h. Then, the mixture was poured into water, and the aqueous layer was extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:2 to 2:3) to give 1.72 g (81%) of the title compound as a colorless oil.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:2 to 2:3)

Sources & evidence

ORD record
ord-19bb2885b4e44639a726220442ddf661
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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