HCID 15157459, compound → HCID 15157491, compound
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]=[C:8]1[C:13]2[CH:14]=[CH:15][C:16]([O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[C:35]4[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=4[CH:29]=[CH:28][CH:27]=3)=[C:17]([CH2:18][CH2:19][CH3:20])[C:12]=2[O:11][C:10]([CH2:43][CH2:44][C:45](OCC)=[O:46])([CH2:36][CH2:37][C:38](OCC)=[O:39])[CH2:9]1>O1CCCC1>[OH:7][CH:8]1[C:13]2[CH:14]=[CH:15][C:16]([O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[C:35]4[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=4[CH:29]=[CH:28][CH:27]=3)=[C:17]([CH2:18][CH2:19][CH3:20])[C:12]=2[O:11][C:10]([CH2:36][CH2:37][CH2:38][OH:39])([CH2:43][CH2:44][CH2:45][OH:46])[CH2:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred suspension of 319 mg (8.40 mmol) of LiAlH4 in 12 ml of tetrahydrofuran (THF) at 0° C. was added a solution of 1.00 g (1.68 mmol) of the title product of Example 42 in 5 ml of tetrahydrofuran. After one-half hour, the mixture was permitted to warm to room temperature, and stirred further for two hours. The reaction was then quenched by sequentially adding 320 μl of water, 320 μl of 15% aqueous sodium hydroxide, and 960 μl of water. The formed salts were removed by filtration, and the solvent removed under reduced pressure to give the title compound (770 mg) as a white solid, m.p. 123°-123.5° C.
Workup
- waitAfter one-half hour
- customThe reaction was then quenched
- additionby sequentially adding 320 μl of water, 320 μl of 15% aqueous sodium hydroxide, and 960 μl of water
- customThe formed salts were removed by filtration
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-afea22df382542d7b9f14083f86927e4
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05093353
Reaction notes
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