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

HRID 473096Notes

Reaction equation

HRID 473096 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]([NH:17][CH:18]1[C:26]2[C:21](=[CH:22][C:23]([C:27](OC)=[O:28])=[CH:24][CH:25]=2)[CH2:20][CH2:19]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[OH:28][CH2:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[CH:18]([NH:17][C:15](=[O:16])[O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:19][CH2:20]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67088132methyl 1-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 67088218Benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., LiAlH4 (2.4 M, 5.2 mL, 12.5 mmol) was added gradually to a solution of methyl 1-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (3.87 g, 11.9 mmol) in anhydrous THF (50 mL). The reaction was stirred for 1.5 h before being quenched by sequentially adding of water (450 μL), of 1 N NaOH (450 μL), and water (900 μL). The mixture was stirred for 10 minutes. Sodium sulfate was added and the mixture was filtered to remove insoluble salts. The residue was washed with ethyl acetate. The combined organic filtrates were evaporated to dryness in vacuo. The off-white residue was triturated with diethyl ether to afford the title compound as an off white solid (2.53 g, 71.5%). MS (ESI): m/z [M+NH4]+ 315.0

Workup

  1. custombefore being quenched
  2. additionby sequentially adding of water (450 μL), of 1 N NaOH (450 μL), and water (900 μL)
  3. stirringThe mixture was stirred for 10 minutes
  4. additionSodium sulfate was added
  5. filtrationthe mixture was filtered
  6. customto remove insoluble salts
  7. washThe residue was washed with ethyl acetate
  8. customThe combined organic filtrates were evaporated to dryness in vacuo
  9. customThe off-white residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-ca263934d37a4eeeaf15af2556fbc936
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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