Benzene → HCID 22867075, compound

HRID 1901159Notes

Reaction equation

HRID 1901159 reaction equation
[CH3:1][C@H:2]([NH2:11])[C@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O=[C:13]([CH3:27])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:26][O:25][C:23]([CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:13]([NH:11][C@@H:2]([CH3:1])[C@@H:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[OH:10])[CH3:27])=[CH:21][CH:20]=1)=[O:24]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10297PhenylpropanolamineHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 22867075HCID 22867075, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 3 g of (1R,2S)-(-)-norephedrine, 4.36 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 60 ml of benzene, 50 ml of absolute methanol and 3.41 g of sodium cyanoborohydride, 2.65 g of the title compound were obtained as crystals, melting at 124° C. (after recrystallization from a mixture of ethyl acetate and hexane).

Sources & evidence

ORD record
ord-a2a42550ca0d4ee698588bf90e667d18
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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