Methanol → (1R*,2R*,4'S*,5S*,6R*)-2',3',4',5'-Tetrahydro-4'-(2-methoxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

HRID 1017282Notes

Reaction equation

HRID 1017282 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[C@H:13]1[CH2:17][O:16][C@:15]2([CH2:23][CH2:22][C@@H:21]3[NH:24][C@@:18]2([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:19][C@H:20]3[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:14]1.N(C(OCC)=O)=N[C:42](OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>O1CCCC1>[CH3:42][O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:10])[F:11])=[CH:4][C:3]=1[C@H:13]1[CH2:17][O:16][C@:15]2([CH2:23][CH2:22][C@@H:21]3[NH:24][C@@:18]2([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:19][C@H:20]3[S:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH2:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70152267(1R*,2R*,4'S*,5S*,6R*)-2',3',4',5'-Tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Product 1

HCID 70152315(1R*,2R*,4'S*,5S*,6R*)-2',3',4',5'-Tetrahydro-4'-(2-methoxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of (1R*,2R*,4S*,5S*,6R*)-2′,3′,4′,5′-tetrahydro-4′-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Example 10; 60 mg, 0.11 mmol), diethyl azodicarboxylate (0.04 ml, 0.25 mmol), triphenylphosphine (68 mg, 0.26 mmol), methanol (0.2 ml) and tetrahydrofuran (2 ml) was stirred at room temperature overnight then concentrated in vacuo and treated with methanol (2 ml) followed by 4M aqueous Na

Workup

  1. concentrationthen concentrated in vacuo
  2. additiontreated with methanol (2 ml)

Sources & evidence

ORD record
ord-49ecc270a6f4499b9e4e47e4e470f6ff
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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