Sodium cyanoborohydride → 5-Acetylamino-2-(1-phenylethylamino)-tetraline

HRID 1614273Notes

Reaction equation

HRID 1614273 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=O)[CH2:10]2)(=[O:3])[CH3:2].Cl.[C:17]1([C@H:23]([NH2:25])[CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([NH:25][CH:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:24])[CH2:10]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 12236043(R)-1-phenylethylamine hydrochlorideHCID 148364565-Acetylamino-2-tetralone

Product 1

HCID 148365735-Acetylamino-2-(1-phenylethylamino)-tetraline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Starting from 16.24 g (0.08 mol) of 5-acetylamino-2-tetralone, 240 ml of methanol, 19.0 g (0.12 mol) of (R)-1-phenylethylamine-hydrochloride and 6.0 g (0.096 mol) of sodium cyanoborohydride, the title compound is obtained analogously to Example 4.1.11 and is crystallised from 75 ml of toluene. Yield 18.5 g (74.9% of theory), melting point 158° C. It consists of approximately equal parts of the (R/R)- and (S/R)-diastereoisomers.

Sources & evidence

ORD record
ord-144797a8ca3f40acb26de6f610413971
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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