Borane → HCID 44303835, compound

HRID 2226612Notes

Reaction equation

[CH2:1]([N:6]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[N:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([C:30](O)=[O:31])[CH2:10]1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].B>C1COCC1>[CH2:33]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[N:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([CH2:30][OH:31])[CH2:10]1)=[O:8])[CH2:34][CH2:35][CH2:36][CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

1.24 g (2.44 mmole) of (S)-4-(dipentylcarbamoyl)-1-(diphenylcarbamoyl)piperazine-2-carboxylic acid dissolved in 6 ml of THF was cooled to 0° C. in an ice bath. To this 9 ml (9 mmole) of 1.0M borane solution in THF was slowly added during a 15 min. period. The resulting mixture was stirred for 24 hr at 25°. The excess hydride was destroyed carefully with 20 ml of a 1:1 mixture of THF and water. The aqueous phase was saturated with anhydrous potassium carbonate. The THF layer was separated and aqueous layer was extracted with ether. The combined organic phase was dried over magnesium sulfate. The solvents were removed on a rotary evaporator to yield 1.18 g (98%) of (S)-4-(dipentylcarbamoyl)-1-(diphenylcarbamoyl)-2-(hydroxymethyl)piperazine as a white solid, mp 133°-134°.

Workup

customThe excess hydride was destroyed carefully with 20 ml of a 1:1 mixture of THF and water
customThe THF layer was separated
extractionaqueous layer was extracted with ether
dry with materialThe combined organic phase was dried over magnesium sulfate
customThe solvents were removed on a rotary evaporator

Sources & evidence

ORD record: ord-e3271a07c5c143d2a7a6fae978616e94
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348955

Reaction notes

Loading…