Hexane → HCID 21645459, compound

HRID 1493398Notes

Reaction equation

HRID 1493398 reaction equation
[C:1]([N:5]1[CH2:9][CH2:8][O:7][P:6]1Cl)([CH3:4])([CH3:3])[CH3:2].[OH:11][CH:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[N:15]([O:20][CH:21]([CH3:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]([CH3:30])([CH3:29])[CH2:13]1.C(N(CC)CC)C.CCCCCC>O1CCCC1>[C:1]([N:5]1[CH2:9][CH2:8][O:7][P:6]1[O:11][CH:12]1[CH2:17][C:16]([CH3:18])([CH3:19])[N:15]([O:20][CH:21]([CH3:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]([CH3:29])([CH3:30])[CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 12068227HCID 12068227, compoundHCID 142281093-tert-Butyl-2-chloro-1,3,2-oxazaphospholidine

Product 1

HCID 21645459HCID 21645459, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9.8 grams (54 mmol) of 3-tert-butyl-2-chloro-1,3,2-oxazaphospholidine in 40 ml of tetrahydrofuran is added dropwise over 30 minutes to a solution of 15.0 grams (54 mmol) of 4-hydroxy-1-alpha-methylbenzyloxy-2,2,6,6-tetramethylpiperidine, prepared in Example 2A, 6.0 grams (159 mmol) of triethylamine and 80 ml of tetrahydrofuran. The reaction temperature increases from 20° C. to 32° C. during the addition. The reaction mixture is stirred for three hours after the addition is complete. Triethylamine hydrochloride is removed by filtration, and the filtrate is concentrated under reduced pressure to yield an oil. Trituration of the crude product with hexane affords 9.3 grams (41% yield) of the title compound as a white solid melting at 110-113° C.

Workup

  1. temperatureThe reaction temperature increases from 20° C. to 32° C. during the addition
  2. additionafter the addition
  3. customTriethylamine hydrochloride is removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto yield an oil

Sources & evidence

ORD record
ord-f7f358b5aef748feaa9f0f65e9923e12
Source dataset
uspto-grants-1991_06
Patent number
US05021481

Reaction notes

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