Triphenylphosphine → tert-Butyl (1S,3R)-3-(6-bromopyridin-2-yloxy)cyclohexylcarbamate

HRID 1775103Notes

Reaction equation

HRID 1775103 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]1.[Br:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33](O)[N:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:30][C:31]1[N:32]=[C:33]([O:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH2:17]2)[CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 29949049t-Butyl ((1S,3S)-3-hydroxycyclohexyl)carbamateHCID 178515930HCID 178515930, compound

Product 1

HCID 86676699tert-Butyl (1S,3R)-3-(6-bromopyridin-2-yloxy)cyclohexylcarbamateYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.473 mL (2.4 mmol) of diisopropylazodicarboxylate in 2 ml of tetrahydrofuran was added dropwise to a mixture of 454 mg (2.0 mmol) of tert-butyl (1S,3S)-3-hydroxycyclohexylcarbamate, 418 mg (2.40 mmol) of 2-bromo-6-hydroxypyridine and 629.5 mg (2.4 mmol) of triphenylphosphine in 5 ml of tetrahydrofuran at 0-5° C. The mixture was stirred for 18 hours. The mixture was concentrated, the residue purified via silica gel chromatography using a gradient of ethyl acetate in heptane to afford 222 mg (30%) of tert-Butyl (1S,3R)-3-(6-bromopyridin-2-yloxy)cyclohexylcarbamate. ESI MS m/z 370.9 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified via silica gel chromatography

Sources & evidence

ORD record
ord-b5bfe7a3c9b24a59b972ce9ef9c27240
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…