Aluminium lithium hydride → (S)-benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 473107Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][C:22]3[CH:23]=[C:24]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=3)[C:25](OC)=[O:26])[CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:26][CH2:25][C:24]1[CH:23]=[C:22]([CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=1)[CH2:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:20]2

Participants

Conditions

Temperature: 0 °C

Procedure

To (S)-methyl 3-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate (2.90 mmol, 1.4 g) at 0° C. in THF (29.0 mL) under an argon atmosphere was added Lithium aluminium hydride in THF (2.90 mmol, 2.90 mL) dropwise. The reaction was left to stir for 1.5 hrs at 0° C. The reaction was quenched with MeOH before the addition of 5N HCl (aq) to adjust the pH to 3. The reaction mix was diluted with DCM before washing with water (×1) followed by brine (×1). The DCM layer was dried over MgSO4 before removing the solvent in vacuo to give the product as a clear glassy solid (1.34 g, 102%). MS (ESI): m/z [M+H]+ 456.1

Workup

waitThe reaction was left
customThe reaction was quenched with MeOH before the addition of 5N HCl (aq)
additionThe reaction mix
additionwas diluted with DCM
washbefore washing with water (×1)
dry with materialThe DCM layer was dried over MgSO4
custombefore removing the solvent in vacuo

Sources & evidence

ORD record: ord-5685eb2f825f4b42ad88ab570444cc70
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

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