Sodium borohydride → HCID 59201577, compound

HRID 451686Notes

Reaction equation

HRID 451686 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([O:23][CH2:24][C:25](OCC)=[O:26])[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1.[BH4-].[Na+]>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([O:23][CH2:24][CH2:25][OH:26])[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59201428HCID 59201428, compound

Product 1

HCID 59201577HCID 59201577, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3R)-tert-butyl 3-((2,3-difluorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate (4 g, 9.7 mmol) in MeOH (80 mL) was added NaBH4 (2.9 g, 77.4 mmol) in portions while the temperature was lower than 40° C. After addition, the mixture was stirred at rt for 2-3 hrs. The solvent was removed in vacuo to give a residue, which was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and evaporated to give (3R)-tert-butyl 3-((2,3-difluorophenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate (3.5 g, 97%). 1H NMR (CDCl3, 400 MHz) δ 7.12 (m, 3H), 4.52 (q, 1H), 4.11 (m, 1H), 3.69 (m, 3H), 3.41 (m, 3H), 2.65 (m, 1H), 2.02 (m, 1H), 1.65 (m, 1H), 1.42 (d, 9H).

Workup

  1. customwas lower than 40° C
  2. additionAfter addition
  3. customThe solvent was removed in vacuo
  4. customto give a residue, which
  5. customwas partitioned between water and ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-e550346684f848dca7dfe0bb043d4c99
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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