Potassium Bromide → Methyl (2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoate--hydrogen chloride (1/1)

HRID 1647763Notes

Reaction equation

HRID 1647763 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:29])[CH:5]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][N:7]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)([CH3:13])[CH:9]([CH3:21])[CH2:8]1.Cl.COC(=O)C(CC1C=CC=CC=1)CN1CCCCC1.O.OC1C=C(C2(C)CCN(CC(CC3C=CC=CC=3)C(O)=O)CC2C)C=CC=1.[K+].[Br-]>>[ClH:1].[CH3:2][O:3][C:4](=[O:29])[C@@H:5]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][N:7]1[CH2:12][CH2:11][C@:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)([CH3:13])[C@@H:9]([CH3:21])[CH2:8]1

Participants

5

Reactant 4

HCID 253877Potassium BromideHCID 67690602HCID 67690602, compoundHCID 77703780HCID 77703780, compoundHCID 86748793HCID 86748793, compound

Product 1

HCID 9909905Methyl (2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoate--hydrogen chloride (1/1)

Procedure

Purity: 96.2% ((αS, 3R, 4R) -4-(3-hydroxyphenyl)-3,4-dimethyl-α- (phenylmethyl)-1-piperidinepropanoic acid methyl ester hydrochloride, 2.9% (αR, 3R, 4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-(α-(phenylmethyl)-1-piperidinepropanoic acid methyl ester hydrochloride and 0.7% (αS, 3R, 4R)-4-(3-hydroxyphenyl)-3,4 -dimethyl-α-(phenylmethyl)-1-piperidinepropanoic acid monohydrate (HPLC area %). mp 230°-232 ° C. (dec), IR (KBr): 3174, 1732, 1620, 1586, 1276, 785,749, 706 cm-1. 1H-NMR (DMSO-d6): d [0.78 (d, 0.85 ×3H, J=7.2 Hz) & 1.02 (d, 0.15×3H, J=7.2 Hz), diastereomeric salts], [1.28 (s, 0.15×3H), 1.34 (s, 0.85×3H), diastereomeric salts], 1.76 (br d, 1H), 2.10-2.48 (m, 2H), 2.75-3.65 (m, 12H), 6.60-6.90 (m, 3H), 7.11 (t, 1H, J=7.8 Hz), 7.15-7.35 (m, 5H), 9.43 (br s, 1H), 9.75 (br s, 1H).

Sources & evidence

ORD record
ord-f44dd1ccac774961b6b89a060a4c645e
Source dataset
uspto-grants-1995_07
Patent number
US05434171

Reaction notes

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