Sodium borohydride → HCID 89524756, compound

HRID 1621011Notes

Reaction equation

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

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 89525991HCID 89525991, compound

Product 1

HCID 89524756HCID 89524756, compoundYield 15%

Conditions

Temperature: 0 °C

Procedure

To a solution of Example 253B (0.19 g, 0.0007 mol) was added NaBH4 (0.03 g, 0.84 mmol) in small portions at 0° C. The minxture was stirred at 0° C. for 1 hour, and concentrated. The residure was purified by Prep. TLC on silica gel and eluted with petroleum ether/EtOAc (5:1) to give the title compound (total yiled for 3 steps 15%). MS: m/z 268 (M+H); 1H NMR (400 MHz, CDCl3) δ 8.58 (d, J=4.8 Hz, 1H), 7.66 (m, 1H), 7.23 (m, 5H), 4.94 (s, 1H), 4.63 (b, 1H), 2.79 (d, J=14.0 Hz, 1H), 2.27 (d, J=14.0 Hz, 1H), 2.17 (m, 2H), 2.12 (s, 3H), 1.90 (m, 2H), 1.56 (m, 2H).

Workup

concentrationconcentrated
customThe residure was purified by Prep
washTLC on silica gel and eluted with petroleum ether/EtOAc (5:1)

Sources & evidence

ORD record: ord-b36e9df08acf4543adc26cf93847dbaf
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772500B2

Reaction notes

Loading…