Borane;tetrahydrofuran → HCID 68442993, compound

HRID 2246979Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@@H:11]([CH2:42][CH2:43][C:44](=[O:46])[CH3:45])[CH2:10]2)=[CH:5][CH:4]=1.B.O1CCCC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:33])=[O:34])[C@@H:11]([CH2:42][CH2:43][CH:44]([OH:46])[CH3:45])[CH2:10]2)=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 68442728HCID 68442728, compound

Product 1

HCID 68442993HCID 68442993, compound

Procedure

Similar to procedure 29a, 800 mg of 4-[(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-butan-2-one and 3.0 ml of borane-tetrahydrofuran complex (1N in tetrahydrofuran) are used to afford the title compound as a yellow oil. Rf=0.22 (EtOAc-heptane 2:1); Rt=5.00.

Sources & evidence

ORD record: ord-87f1d8341f604243bba18f16384ad6e8
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687495B2

Reaction notes

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