Sodium borohydride → (5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanol

HRID 1630968

Reaction equation

[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH3:18])=[C:8]([CH:11]=1)[CH:9]=[O:10]>CO.[NH4+].[Cl-]>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH3:18])=[C:8]([CH2:9][OH:10])[CH:11]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Sodium borohydride (2.2 g, 57.8 mmol) was added portion-wise into a solution of 5-bromo-2-(2-methylpiperidin-1-yl)benzaldehyde (16.3 g, 57.8 mmol) in MeOH (300 mL) cooled at 5° C. After 30 min, the reaction mixture was diluted with a saturated aqueous solution of NH4Cl (300 mL) and extracted with EtOAc (600 mL+300 mL). The organic layers were washed with a saturated aqueous solution of NH4Cl (150 mL) and brine (300 mL). The organic layers were combined, dried (MgSO4) and the solvents were removed under reduced pressure to give the title compound as a yellow oil (15.9 g, 97%) used without further purification in the next step. HPLC (Method A), Rt 2.1 min (Purity: 94.9%). UPLC/MS, M+(ESI): 284.1, 286.0. 1H NMR (CDCl3, 300 MHz) δ 7.38 (dd, J=8.5, 2.4 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.13 (d, J=8.5 Hz, 1H), 6.40 (brs, 1H), 4.86 (d, J=13.9 Hz, 1H), 4.67 (d, J=13.9 Hz, 1H), 3.06-2.88 (m, 2H), 2.61 (td, J=11.4, 3.2 Hz, 1H), 1.88-1.58 (m, 4H), 1.53-1.32 (m, 2H), 0.90 (d, J=6.2 Hz, 3H).

Workup

extractionextracted with EtOAc (600 mL+300 mL)
washThe organic layers were washed with a saturated aqueous solution of NH4Cl (150 mL) and brine (300 mL)
dry with materialdried (MgSO4)
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-b559cc17ebc64fb9ae8e7d22fbd0cf52
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Linked notes

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