Ethanol → HCID 86742919, compound

HRID 620322Notes

Reaction equation

HRID 620322 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[C@@H:12]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23])[CH2:13][N+:14]([O-])=O)[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>[NH2:14][CH2:13][C@H:12]([C@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[OH:23])[C:11]1[CH:24]=[CH:25][CH:26]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 53937507HCID 53937507, compound

Product 1

HCID 86742919HCID 86742919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 106.6 g (0.3 mol) of rac-(2S*)-2-[(R*)-3-(benzyloxy)-α-(nitromethyl)benzyl]cyclohexanone in 500 ml of dry tetrahydrofuran is added drowpise while stirring within about 3 hours 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 55°. The reaction mixture is stirred at 50° overnight, treated, after cooling, with 40 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 residue is crystallized from methylene chloride/isopropyl ether, there being obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-3-(benzyloxy)benzyl]cyclohexanol in the form of colourless crystals of m.p. 139°-141°.

Workup

  1. customdoes not exceed 55°
  2. additiontreated
  3. filtrationthe separated precipitate is filtered off under suction
  4. washwhile washing with methylene chloride
  5. customthe filtrate is evaporated
  6. customThe residue is crystallized from methylene chloride/isopropyl ether, there

Sources & evidence

ORD record
ord-20d13969dfe9413c87291dcd6d4dfd12
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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