Water → cis-3-Hydroxymethyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600725Notes

Reaction equation

HRID 600725 reaction equation
C([O:3][C:4]([C:6]1[C@@H:10]2[CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][C@@H:9]2[O:8][N:7]=1)=O)C.[BH4-].[Na+].O>C(O)C>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]2[C@H:10]([C:6]([CH2:4][OH:3])=[N:7][O:8]2)[CH2:11]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 16098104Cis-5-Tert-Butyl3-Ethyl6,6A-Dihydro-3Ah-Pyrrolo[3,4-D]Isoxazole-3,5(4H)-Dicarboxylate

Product 1

HCID 68971833cis-3-Hydroxymethyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To ester 6 (1.50 g; 5.29 mmol) in ethanol (50 mL) at 0° C., was added sodium borohydride (1.57 g; 41.5 mmol) in several portions. The reaction mixture was stirred at 0° C. for 30 minutes and then at room temperature for 3 hours. The reaction mixture was carefully added to water (150 mL) and extracted with methylene chloride (3×100 mL). The combined organic layers were washed with several portions of water, brine, dried (MgSO4), filtered and evaporated to yield alcohol 7 as a white solid.

Workup

  1. waitat room temperature for 3 hours
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washThe combined organic layers were washed with several portions of water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e5c6793641bc4592af42ad36632022de
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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