Aluminium lithium hydride → HCID 118308200, compound

HRID 1750494Notes

Reaction equation

HRID 1750494 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:14][C:15](=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:22]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:14][CH3:15])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118308250HCID 118308250, compound

Product 1

HCID 118308200HCID 118308200, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-(dibenzylamino)cyclopentyl]carbamate (320 mg, 0.841 mmol) in THF (2.8 ml) at room temperature was added drop wise lithium aluminium hydride in THF (1 M, 1.3 ml, 1.261 mmol). The reaction was stirred for 1 hour and then was heated to 60° C. for 3 hours. The reaction was then cooled to room temperature and quenched by the addition of sodium sulfate decahydrate, filtered and washed with THF and ethyl acetate. The filtrate was concentrated in vacuo to afford the title compound.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customquenched by the addition of sodium sulfate decahydrate
  3. filtrationfiltered
  4. washwashed with THF and ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4742801dbf774d0eae1443feaee46005
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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