Tetrahydrofuran → HCID 66661961, compound

HRID 557916Notes

Reaction equation

HRID 557916 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([N:14]3[CH2:18][CH2:17][C@@:16]4([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[C:20](=[O:27])[O:19]4)[CH2:15]3)=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[N:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([N:14]3[CH2:18][CH2:17][C@@:16]4([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[C:20](=[O:27])[O:19]4)[CH2:15]3)=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66662373HCID 66662373, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 66661961HCID 66661961, compound

Procedure

To a mixture of (1R)-1′-({1-[4-(hydroxymethyl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (16.0 mg, 0.0000440 mol, prepared in example 237), triphenylphosphine (17 mg, 0.000066 mol), and 2-hydroxypyridine (4.0 mg) in tetrahydrofuran (2 mL, 0.02 mol) was added diisopropyl azodicarboxylate (14 μL, 0.000070 mol) at room temperature, and the mixture was stirred overnight. The product was isolated and purified by prep-HPLC. LC-MS: 441.2 (M+H+)

Workup

  1. customThe product was isolated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-2a56a404bb0a4a0596d654e697689e30
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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