Tetrahydrofuran → HCID 66662572, compound

HRID 504330Notes

Reaction equation

HRID 504330 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C@@:15]4([C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[C:19](=[O:26])[O:18]4)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:27]1[CH2:32][CH2:31][CH:30](O)[CH2:29][CH2:28]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>>[O:27]1[CH2:32][CH2:31][CH:30]([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]([N:13]4[CH2:17][CH2:16][C@@:15]5([C:25]6[CH:24]=[CH:23][N:22]=[CH:21][C:20]=6[C:19](=[O:26])[O:18]5)[CH2:14]4)=[O:12])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66662080HCID 66662080, compound

Product 1

HCID 66662572HCID 66662572, compoundYield 17.6%

Procedure

A mixture of (1R)-1′-{[1-(4-hydroxyphenyl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (10 mg, 0.00003 mol), tetrahydro-4H-pyran-4-ol (6.5 μL, 0.000068 mol), diisopropyl azodicarboxylate (13 μL, 0.000068 mol), and triphenylphosphine (18 mg, 0.000068 mol) in tetrahydrofuran (200 μL, 0.002 mol) was stirred at room temperature overnight. It was purified with prep-HPLC to afford 2.3 mg of product. LCMS: m/z 435.1 (M+H)+.

Workup

  1. customIt was purified with prep-HPLC

Sources & evidence

ORD record
ord-d51391a91270407abdd7e4b5e253bcab
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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