Triphenylphosphine → HCID 57300936, compound

HRID 843445Notes

Reaction equation

HRID 843445 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[C@@H:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34]CC=C)=[CH:30][CH:29]=2)[C@H:10]([O:38][CH2:39][C@H:40]([OH:44])[CH2:41][O:42][CH3:43])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[BH4-].[Li+]>O1CCCC1.CC(O)=O.CC(O)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[C@@H:11]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[C@H:10]([O:38][CH2:39][C@H:40]([OH:44])[CH2:41][O:42][CH3:43])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 4148881Lithium borohydrideHCID 57269223(3S,4R,5R)-4-(4-allyloxy-phenyl)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57300936HCID 57300936, compound

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 11(c) the (3S,4R,5R)-4-(4-allyloxy-phenyl)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester was treated with palladium-II-acetate, triphenylphosphin and lithiumborohydride in tetrahydrofuran to yield the (3S,4R,5R)-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-4-(4-hydroxy-phenyl)-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as colorless oil; MS: 568 (M+H)+.

Sources & evidence

ORD record
ord-f9340792586e4768ac724c4f00216b97
Source dataset
uspto-grants-2002_04
Patent number
US06376672B1

Reaction notes

Loading…