1-Octanol → HCID 57554732, compound

HRID 1511858Notes

Reaction equation

HRID 1511858 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:17][CH2:16][C@@:10]3([NH:14][C:13](=[O:15])[O:12][CH2:11]3)[CH2:9]2)=[CH:4][CH:3]=1.[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:17][CH2:16][C@@:10]3([NH:14][C:13](=[O:15])[O:12][CH2:11]3)[CH2:9]2)=[CH:4][CH:3]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 57554654HCID 57554654, compound

Product 1

HCID 57554732HCID 57554732, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (5R,7R)-7-(4-hydroxy-phenyl)-3-oxa-1-aza-spiro[4.4]nonan-2-one (75 mg, 0.32 mmol), octanol (55.6 μL, 0.35 mmol) and resin bound triphenylphosphine (343 mg, 2 mmol/g, 0.70 mmol) in THF (4.0 mL) was cooled to about 0° C. and di-tert-butyl azodicarboxylate (80.5 mg, 0.35 mmol) was added dropwise. The reaction was allowed to warm up to room temperature for about 3 hours, then the resin was filtered off and washed with DCM (10 mL). The filtrates were combined and concentrated. The crude product was purified on silica gel using a gradient of 30% to 60% EtOAc in heptane. Pure fractions were combined and concentrated to yield 67.0 mg (61%) of (5R,7R)-7-(4-octyloxy-phenyl)-3-oxa-1-aza-spiro[4.4]nonan-2-one as a white solid.

Workup

  1. filtrationthe resin was filtered off
  2. washwashed with DCM (10 mL)
  3. concentrationconcentrated
  4. customThe crude product was purified on silica gel using a gradient of 30% to 60% EtOAc in heptane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0cef66b109c54a3aaad540d027206bb6
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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