Sodium borohydride → N-[2-t-Butyl-5-(6-hexyl-5-hydroxyhexyl)phenyl]-2-(9H-xanthen-9-yl)acetamide
Reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:25])[CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:9][C:8]=1[NH:26][C:27](=[O:43])[CH2:28][CH:29]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[O:36][C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)([CH3:6])([CH3:5])[CH3:4]>>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:9][C:8]=1[NH:26][C:27](=[O:43])[CH2:28][CH:29]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=2[O:36][C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)([CH3:4])([CH3:5])[CH3:6]Participants
3
Procedure
37 mg (0.99 mmol) of sodium borohydride were added to 10 ml of a methanolic suspension containing 544 mg (0.986 mmol) of N-[2-t-butyl-5-(6-cyclohexyl-5-oxohexyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 21), in an ice bath. The ice bath was then removed, and the reaction mixture was stirred for 1 hour at room temperature. At the end of this time, the reaction solution was diluted with diethyl ether, washed with a saturated aqueous solution of ammonium chloride and then with water several times. The solvent was then removed by distillation under reduced pressure, to obtain 532 mg (yield 97%) of the title compound as a foam-like substance.
Workup
- customThe ice bath was then removed
- additionAt the end of this time, the reaction solution was diluted with diethyl ether
- washwashed with a saturated aqueous solution of ammonium chloride
- customThe solvent was then removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-8497c46b66224ed8b878b5d1300d4024
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05534529
Reaction notes
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