Ethanol → HCID 54216346, compound

HRID 620316Notes

Reaction equation

HRID 620316 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C@@H:6]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])[CH2:7][N+:8]([O-])=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.O1CCCC1.O>O1CCCC1.CCOCC>[NH2:8][CH2:7][C@H:6]([C@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[OH:17])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 54230375HCID 54230375, compound

Product 1

HCID 54216346HCID 54216346, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 112 g (0.4 mol) of rac-(2S*)-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanone in 1 l of dry tetrahydrofuran is added dropwise under argon to a suspension of 39 g (1.03 mol) of lithium aluminium hydride in 1 l of dry tetrahydrofuran so that the temperature does not exceed 50°, whereupon the reaction mixture is stirred at 50° overnight. After cooling to room temperature the reaction mixture is treated with 50 ml of ethanol and subsequently with 200 ml of tetrahydrofuran/water (1:1), the separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The oil obtained is dissolved in 1 l of ether and the solution is left to stand at room temperature overnight. The separated colourless crystals are filtered off under suction, there being obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclohexanol of m.p. 108°-110°. The rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclohexanol hydrochloride prepared from the base in the usual manner is recrystallized from ethanol/ether and melts at 259°-260° (decomposition).

Workup

  1. customdoes not exceed 50°, whereupon the reaction mixture
  2. filtrationthe separated precipitate is filtered off under suction
  3. washwhile washing with methylene chloride
  4. customthe filtrate is evaporated
  5. customThe oil obtained
  6. waitthe solution is left
  7. waitto stand at room temperature overnight
  8. filtrationThe separated colourless crystals are filtered off under suction, there

Sources & evidence

ORD record
ord-59bc38e6ce5d4682bcabfb54ef5a3cf4
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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