Hydrochloric Acid → HCID 86742921, compound

HRID 620324Notes

Reaction equation

HRID 620324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C@@H:6]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17])[CH2:7][N+:8]([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[ClH:32]>O1CCCC1.O1CCCC1.O>[ClH:32].[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:18]=[CH:19][C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 54357703HCID 54357703, compound

Product 1

HCID 86742921HCID 86742921, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 50.5 g (163 mmol) of rac-(2S*)-2-[(R*)-3,4-dimethoxy-α-(nitromethyl)benzyl]cyclohexanone in 500 ml of dry tetrahydrofuran is added dropwise while stirring to a suspension of 15.4 g (407 mmol) of lithium aluminium hydride in 350 ml of dry tetrahydrofuran under argon so that the temperature does not exceed 50°. The reaction mixture is stirred at 50° overnight and treated, after cooling, firstly with ethanol and subsequently with tetrahydrofuran/water (1:1). The separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The oily crude product obtained is converted into the hydrochloride which is recrystallized from alcohol. There is obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-3,4-dimethoxybenzyl]cyclohexanol hydrochloride of m.p. 216°-218°.

Workup

  1. customdoes not exceed 50°
  2. additiontreated
  3. filtrationThe separated precipitate is filtered off under suction
  4. washwhile washing with methylene chloride
  5. customthe filtrate is evaporated
  6. customThe oily crude product obtained
  7. customis recrystallized from alcohol

Sources & evidence

ORD record
ord-4118f24e0c3d4030be082424f1429764
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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