Aluminium lithium hydride → 3-Dibenzylaminocyclohexylmethanol

HRID 1817745Notes

Reaction equation

HRID 1817745 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](OC)=[O:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC1C=CC=CC=1)C1CCCC(C(OCC2C=CC=CC=2)=O)C1)C1C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH2:19]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][OH:16])[CH2:10]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 57882728Methyl 3-dibenzylaminocyclohexanoateHCID 57882731Benzyl 3-dibenzylaminocyclohexanoate

Product 1

HCID 596592093-Dibenzylaminocyclohexylmethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 23 g of a 1:3.5 mixture of methyl 3-dibenzylaminocyclohexanoate and benzyl 3-dibenzylaminocyclohexanoate were added dropwise to a suspension of 4.4 g of LiAlH4 in 250 ml of diethyl ether. The suspension was stirred at 0° C. for 2 h and then quenched using 2 ml of EtOAc, and 10 ml of 10N KOH were added. 50 g of MgSO4 were then added and the suspension was filtered. The residue was digested with EtOAc for 2 h and filtered again. The filtrate was concentrated, giving the product as an oil. C21 H27NO (309.46), LCMS (ESI): 310.2 (MH+).

Workup

  1. customquenched
  2. additionwere added
  3. addition50 g of MgSO4 were then added
  4. filtrationthe suspension was filtered
  5. waitThe residue was digested with EtOAc for 2 h
  6. filtrationfiltered again
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ffc6c51054b14601a7e5820937ed5241
Source dataset
uspto-grants-2009_10
Patent number
US07598281B2

Reaction notes

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