Benzyl Alcohol → HCID 86753769, compound

HRID 1417541Notes

Reaction equation

HRID 1417541 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@@H:28](C(O)=O)[CH2:27][CH2:26][C@@:9]32[O:13][CH2:12][C:11]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])=[CH:10]3)=[CH:4][CH:3]=1.C([N:35]([CH2:39]C)C(C)C)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:48])C=CC=CC=1.[CH2:58]([OH:65])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:58]([O:65][C:39]([NH:35][C@H:28]1[CH2:27][CH2:26][C@:9]2([O:13][CH2:12][C:11]([C:14]3[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=3[O:22][CH:23]([CH3:25])[CH3:24])=[CH:10]2)[C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:48])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86753767HCID 86753767, compound

Product 1

HCID 86753769HCID 86753769, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5R,6S,7S)-6-(4-fluorophenyl)-3-(5-cyano-2-isopropoxy-phenyl)-1-oxaspiro[4.4]non-3-ene-7-carboxylic acid (128 mg, 0.304 mmol) in toluene (2 mL) were added N,N,-diisopropylethylamine (64 μL, 0.367 mmol) followed by diphenylphosphoryl azide (73 μl, 0.339 mmol). The mixture was stirred for 30 minutes at room temperature and then for 1 hour at 100° C. Benzyl alcohol (63 μL, 0.609 mmol) was then added, and the mixture was stirred for 18 hours at 100° C. The cooled mixture was diluted with ethyl acetate (30 mL), washed with saturated sodium hydrogencarbonate solution, saturated brine solution, dried (Na2SO4), and evaporated. Silica gel chromatography eluting with 30% ethyl acetate/hexane afforded the title compound; yield 49 mg. The 400 MHz NMR spectrum in CD3OD was in accord with the desired structure.

Workup

  1. waitfor 1 hour at 100° C
  2. stirringthe mixture was stirred for 18 hours at 100° C
  3. washwashed with saturated sodium hydrogencarbonate solution, saturated brine solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. washSilica gel chromatography eluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-101417fb4a484cc5a234a9371f7170ea
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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