Sodium borohydride → (6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridin-3-yl)methanol

HRID 1474735Notes

Reaction equation

HRID 1474735 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@@H:11]1[CH2:13][C@@H:12]1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][CH2:10][C@@H:11]1[CH2:13][C@@H:12]1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 895818786-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridine-3-carbaldehyde

Product 1

HCID 89584039(6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridine-3-carbaldehyde (1.75 g, 4.50 mmol) was placed in a 250 ml flask and dissolved in MeOH (11.26 ml). Sodium borohydride (0.170 g, 4.50 mmol) was added and the mixture stirred at RT for 1 hour. The mixture was concentrated, dissolved in EtOAc (200 ml) and washed with 1:1 brine:saturated sodium bicarbonate (200 ml). The layers were separated, the aqueous phase extracted with EtOAc (2×70 ml), the organic fractions combined, washed with brine, dried over sodium sulfate filtered, and concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 391 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc (200 ml)
  3. washwashed with 1:1 brine
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with EtOAc (2×70 ml)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1b433b50111416e972aaa22b811ec1b
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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