Tributylstannane → (1R*,2R*,5S*,6R*)-8-Benzyl-2',5'-dihydro-1-phenyl-6-phenylsulfonyl-4'-tributylstannylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

HRID 1017267Notes

Reaction equation

HRID 1017267 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@:10]([C:26]#[C:27][CH2:28]O)([OH:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:36]([SnH:40]([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH3:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C@H:13]2[CH2:12][CH2:11][C@@:10]3([CH:26]=[C:27]([Sn:40]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:28][O:25]3)[C@:9]1([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:15][C@H:14]2[S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70152384(1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

Product 1

HCID 70160343(1R*,2R*,5S*,6R*)-8-Benzyl-2',5'-dihydro-1-phenyl-6-phenylsulfonyl-4'-tributylstannylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]Yield 5.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.26 mmol) was added to a degassed solution of (1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 13; 1.8 g, 3.7 mmol) in tetrahydrofuran (50 ml). The mixture was cooled to +5° C. before tri-n-butyltin hydride (1.3 g, 4.4 mmol) was added. The mixture was allowed to warm to room temperature and stirred for a further 18 hours before triphenylphosphine (1 g, 3.7 mmol) and diethyl azodicarboxylate (0.65 g, 3.7 mmol) were added. After 3 hours the mixture was concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5 and 10% ethyl acetate/iso-hexanes to give the title compound (154 mg, 5.5%).

Workup

  1. additionwas added
  2. additionwere added
  3. concentrationAfter 3 hours the mixture was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 5 and 10% ethyl acetate/iso-hexanes

Sources & evidence

ORD record
ord-aea2ba5e73254e2dae2b145d48d04799
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

Loading…