Aluminium lithium hydride → 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

HRID 2172667Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([C@@H:15]2[CH2:17][C@H:16]2[NH:18][C:19]2[C:20]3[N:31]=[N:30][N:29]([C@H:32]4[C@@H:36]5[O:37][C:38]([CH3:41])([CH3:40])[O:39][C@@H:35]5[C@@H:34]([O:42][CH2:43][C:44](O)=[O:45])[CH2:33]4)[C:21]=3[N:22]=[C:23]([S:25][CH2:26][CH2:27][CH3:28])[N:24]=2)[CH:11]=[CH:12][C:13]=1[F:14]>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([C@@H:15]2[CH2:17][C@H:16]2[NH:18][C:19]2[C:20]3[N:31]=[N:30][N:29]([C@H:32]4[C@@H:36]5[O:37][C:38]([CH3:40])([CH3:41])[O:39][C@@H:35]5[C@@H:34]([O:42][CH2:43][CH2:44][OH:45])[CH2:33]4)[C:21]=3[N:22]=[C:23]([S:25][CH2:26][CH2:27][CH3:28])[N:24]=2)[CH:11]=[CH:12][C:13]=1[F:14]

Participants

Conditions

Temperature: -5 °C

Procedure

LiAlH4 (0.2 g) was added to THF (10 vol) slowly at 0 to −10° C. To this mixture was added a solution of compound 11a (3 g) in THF (15 mL) slowly over 30 min at 0 to −10° C. The reaction mixture was stirred at 0 to −10° C. for 4-12 hrs. The reaction was monitored by TLC. When the reaction was complete, it was quenched and the product was isolated by routine work up. The filtrate was concentrated under reduced pressure, and compound 12 was isolated as an oily mass; yield 14 g, 70-75%.

Workup

customit was quenched
customthe product was isolated by routine work up
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-38c56e67214248f89b31cba28eb5529a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056838B2

Reaction notes

Loading…