Triphenylphosphine → HCID 178443930, compound

HRID 1489482Notes

Reaction equation

HRID 1489482 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([F:34])[C:31]([OH:35])=[C:30]([F:36])[CH:29]=3)[CH2:24][CH2:23]2)[CH2:18][CH2:17]1)[CH2:14][CH3:15].[CH3:37][C@H:38](O)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C1COCC1>[CH2:13]([C@H:16]1[CH2:17][CH2:18][C@H:19]([C@H:22]2[CH2:23][CH2:24][C@H:25]([C:28]3[CH:29]=[C:30]([F:36])[C:31]([O:35][C@H:38]([CH3:37])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[C:32]([F:34])[CH:33]=3)[CH2:26][CH2:27]2)[CH2:20][CH2:21]1)[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2723888(+)-2-OctanolHCID 178448026HCID 178448026, compound

Product 1

HCID 178443930HCID 178443930, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.6 ml (16 mmol) of diethyl azodicarboxylate are added dropwise at room temperature to a mixture of 5 g (15 mmol) of 4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-2,6-difluorophenol, 2.1 g (16 mmol) of (S)-(+)-2-octanol, 4.3 g of triphenylphosphine and 80 ml of THF. The mixture is stirred for 2 hours and subjected to customary work-up. Chromatography gives (R)-(-)-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-1-(1-methylheptyloxy)-2,6-difluorobenzene, C 29 SB 42 Ch 73.8 I, HTP=-7.7, [α]D20 =-6.9 (CH2Cl2).

Sources & evidence

ORD record
ord-3c4636533e074059b210581abb60f3b1
Source dataset
uspto-grants-1997_10
Patent number
US05679282

Reaction notes

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