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

HRID 43017Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21](OC)=[O:22])=[CH:18][CH:19]=2)[CH2:14][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:22][CH2:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:13][CH2:14]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 1-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (5.59 mmol, 1.82 g) in THF (30 mL) at 0° C. was added lithium aluminium hydride (5.59 mmol, 5.59 mL) in a dropwise fashion. Stirring at 0° C. was continued for 1.5 h after which time the reaction mixture was quenched with water and sat Rochelle's salt added followed by DCM & the organics separated/dried (1PS paper) before being concentrated to dryness. The residue was purified by flash chromatography (50 g, 1:1 EtOAc/heptane) to give an off-white solid (800 mg, 2.69 mmol, 48.1%). MS (ESI): m/z [M+H]+ 298.2

Workup

customafter which time the reaction mixture was quenched with water
additionadded
customthe organics separated/dried (1PS paper)
concentrationbefore being concentrated to dryness
customThe residue was purified by flash chromatography (50 g, 1:1 EtOAc/heptane)

Sources & evidence

ORD record: ord-c4106bd6f5f249eea8109b85f1008b14
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536214B2

Reaction notes

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