Methanol → {1-[1-(3-Chlorophenyl)ethyl]cyclobutyl}(pyridin-2-yl)methanol

HRID 1749151Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][C:6]1([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH2:9][CH2:8][CH2:7]1.[BH4-].[Na+].[CH3:23]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([C:6]2([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[OH:11])[CH2:9][CH2:8][CH2:7]2)[CH3:23])[CH:18]=[CH:19][CH:20]=1

Participants

Reactant 3

HCID 887Methanol

HCID 4311764Sodium borohydride

HCID 66749362(1-(3-Chlorobenzyl)cyclobutyl)(pyridin-2-yl)methanone

Product 1

HCID 56653735{1-[1-(3-Chlorophenyl)ethyl]cyclobutyl}(pyridin-2-yl)methanolYield 23.6%

Conditions

Temperature: 0 °C

Procedure

To a solution of Example 44C (0.5 g, 1.67 mmol) in 20 mL of methanol was added NaBH4 (0.076 g, 2 mmol) in small portions at 0° C. The mixture was stirred at 0° C. for 2 h. The mixture was concentrated and the residue was purified by prep TLC (petroleum ether: ethyl acetate=7:1) to afford the title compound (0.35 g, total yield 23.6%). 1H NMR (400 MHz, CDCl3): δ=8.58 (d, J=2.0 Hz, 1H), 7.65-7.62 (m, 1H), 7.27-7.12 (m, 6H), 4.78 (s, 1H), 4.16 (brs, 1H), 3.12-3.00 (m, 1H), 2.17-1.80 (m, 4H), 1.36 (d, J=6.0 Hz, 3H), 1.26-1.17 (m, 1H), 0.95-0.80 (m, 1H). LC-MS: m/z 302 (M+H).

Workup

concentrationThe mixture was concentrated
customthe residue was purified by prep TLC (petroleum ether: ethyl acetate=7:1)

Sources & evidence

ORD record: ord-c0b264ffddb348b0baa02b4f7d78dda5
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156788B2

Reaction notes

Loading…