Aluminium lithium hydride → 5,6,7,8-tetrahydro-2-(phenoxymethyl)-5-(phenylmethyl)-4H-thiazolo[5,4-c]azepine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([CH2:14][C:15]1[S:16][C:17]2[C:18](=O)[N:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:20][CH2:21][CH2:22][C:23]=2[N:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[O:7]([CH2:14][C:15]1[S:16][C:17]2[CH2:18][N:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:20][CH2:21][CH2:22][C:23]=2[N:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1 M solution of lithium aluminium hydride in THF (0.28 mL, 0.28 mmol) was added dropwise to a stirred solution of 5,6,7,8-tetrahydro-2-(phenoxymethyl)-5-(phenylmethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.084 g, 0.23 mmol) in THF (1.8 mL) under N2 at 0° C. The mixture was stirred at room temperature for 1 hour and then quenched with a saturated solution of NH4Cl, diluted with DCM and filtered through a pad of diatomaceous earth. The solvents were evaporated in vacuo to yield 5,6,7,8-tetrahydro-2-(phenoxymethyl)-5-(phenylmethyl)-4H-thiazolo[5,4-c]azepine (0.055 g, 68% yield) as a yellow oil that was used in the next step without further purification. C21H20N2O2S LCMS: Rt 3.02, m/z 365 [M+H]+ (using method, LC-MS Method 6).
Workup
- customquenched with a saturated solution of NH4Cl
- additiondiluted with DCM
- filtrationfiltered through a pad of diatomaceous earth
- customThe solvents were evaporated in vacuo
Sources & evidence
- ORD record
- ord-09526c86e6f7425daab0e6b8b1b9a2ff
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090632B2
Reaction notes
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