Sodium borohydride → Tert-butyl 3,4-bis(hydroxymethyl)piperidine-1-carboxylate

HRID 712500Notes

Reaction equation

HRID 712500 reaction equation
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][CH2:5][CH:4]([C:7](OC)=[O:8])[CH:3]([C:11](OC)=[O:12])[CH2:2]1.[BH4-].[Na+]>CCO>[OH:12][CH2:11][CH:3]1[CH:4]([CH2:7][OH:8])[CH2:5][CH2:6][N:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 867295031-Tert-butyl 3,4-dimethyl piperidine-1,3,4-tricarboxylate

Product 1

HCID 86729504Tert-butyl 3,4-bis(hydroxymethyl)piperidine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-tert-butyl 3,4-dimethyl piperidine-1,3,4-tricarboxylate (4.00 g, 13.30 mmol, 1 eq) in 50 mL of anhydrous EtOH was added NaBH4 (1.26 g, 33.20 mmol, 2.5 eq) in portions at 0° C. The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by a silica gel column chromatography (5:1 (v/v) CH2Cl2/MeOH) to afford the title compound as a white solid (3.00 g, 92.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 246.2 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by a silica gel column chromatography (5:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-7fd140148f6b4ebd94985783c21e247a
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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