N-Hydroxyphthalimide → HCID 86699612, compound

HRID 330961Notes

Reaction equation

HRID 330961 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.O[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[O:27]=[C:18]1[C:19]2[C:20](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:22])[N:17]1[O:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21637085HCID 21637085, compound

Product 1

HCID 86699612HCID 86699612, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ice-cold mixture of tert-butyl (cis-3-hydroxycyclopentyl)methylcarbamate 114 (0.19 g, 0.88 mmol), N-hydroxyphthalimide (0.29 g, 1.78 mmol), and triphenylphosphine (0.46 g, 1.75 mmoL) in tetrahydrofuran (10 mL) was treated with diisopropylazodicarboxylate (0.40 g, 1.98 mmol). The mixture was stirred at room temperature overnight, then concentrated in vacuo to a yellow foam which was purified by chromatography to give 115 (0.19 g, containing DIAD byproduct) as a yellow oil. The mixture was used in the next step without further purification.

Workup

  1. concentrationconcentrated in vacuo to a yellow foam which
  2. customwas purified by chromatography

Sources & evidence

ORD record
ord-eefdc53d1f414ae880211829595bcb1e
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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