Triphenylphosphine → Tert-butyl 4-{[2,6-dichloro-4-(phenylmethoxy)phenoxy]methyl}piperidinecarboxylate

HRID 2242515노트

반응식

HRID 2242515 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cl:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[C:19]([Cl:31])[C:18]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[C:19]([Cl:31])[C:18]=1[O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 120841702,6-Dichloro-4-benzyloxyphenol

생성물 1

HCID 58758910Tert-butyl 4-{[2,6-dichloro-4-(phenylmethoxy)phenoxy]methyl}piperidinecarboxylate수율 97.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of 10.0 grams (0.046 mole) of tert-butyl 4-(hydroxymethyl)piperidinecarboxylate (commercially available) and 12.5 grams (0.046 mole) of 2,6-dichloro-4-(phenylmethoxy)phenol (known compound) in 100 mL of THF was cooled in an ice-water bath and 12.2 grams (0.046 mole) of triphenylphosphine was added in one portion. Upon completion of addition 9 mL (0.046 mole) of diisopropyl azodicarboxylate was added dropwise during a five minute period. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred during an 18 hour period. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 21 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionwas added dropwise during a five minute period
  2. additionUpon completion of addition the reaction mixture
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  4. customThe residue was purified with column chromatography on silica gel
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-360ef681662748d2a871a97b7b6b3075
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671201B2

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