Sodium Hydroxide → HCID 69433610, compound

HRID 1006851Notes

Reaction equation

HRID 1006851 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]([C:11](OCC)=[O:12])[CH2:9][N:8]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[OH:3][CH2:4][CH:6]1[CH2:7][N:8]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:9][CH:10]1[CH2:11][OH:12]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 69429519HCID 69429519, compound

Product 1

HCID 69433610HCID 69433610, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (3RS,4RS)-1-methanesulfonyl-pyrrolidine-3,4-dicarboxylic acid diethyl ester (1.13 g, 3.85 mmol) in THF (40 ml) was slowly added a 1 M solution of LiAlH4 in THF (11.55 ml. 11.55 mmol) at 0° C. The mixture was stirred for 1.5 h at 0° C. Water (0.44 ml), 1 M aqueous NaOH (0.44 ml) and water (1.31 ml) were added subsequently at 0° C. MgSO4 was added and filtered. The solid was washed with EtOAc (4×). The filtrate was evaporated to leave a colorless solid that was washed with hot dichloromethane to give ([3RS,4RS]-4-hydroxymethyl-1-methanesulfonyl-pyrrolidin-3-yl)-methanol as a colorless solid, MS: 268 (M+OAc)−.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with EtOAc (4×)
  3. customThe filtrate was evaporated
  4. customto leave a colorless solid
  5. washthat was washed with hot dichloromethane

Sources & evidence

ORD record
ord-385b3494b6ab43458e2cb969ea76f680
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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