Ethanol → HCID 86742920, compound

HRID 620323Notes

Reaction equation

HRID 620323 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([C@@H:13]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=[O:24])[CH2:14][N+:15]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.O1CCCC1.O>O1CCCC1>[NH2:15][CH2:14][C@H:13]([C@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[OH:24])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 54418106HCID 54418106, compound

Product 1

HCID 86742920HCID 86742920, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 106.6 g (0.33 mol) of rac-(2S*)-2-[(R*)-4-(benzyloxy)-α-(nitromethyl)benzyl]cyclohexanone in 500 ml of dry tetrahydrofuran is added dropwise while stirring to a suspension of 28.6 g (0.75 mol) of lithium aluminium hydride in 500 ml of dry tetrahydrofuran under argon so that the temperature does not exceed 50°. The reaction mixture is stirred at 50° overnight and it is treated, after cooling to room temperature, with 300 ml of ethanol and subsequently with 100 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 crystalline product obtained is recrystallized from methylene chloride/isopropyl ether. There is obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-(benzyloxy)benzyl]cyclohexanol in the form of colourless crystals of m.p. 160°-161°.

Workup

  1. customdoes not exceed 50°
  2. additionit is treated
  3. filtrationThe separated precipitate is filtered off under suction
  4. washwhile washing with methylene chloride
  5. customthe filtrate is evaporated
  6. customThe crystalline product obtained
  7. customis recrystallized from methylene chloride/isopropyl ether

Sources & evidence

ORD record
ord-5fa86327d2b842519bd030d86ac3929f
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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