Ytterbium → tert-Butyl piperazine-1-carboxylate

HRID 891049

Reaction equation

HRID 891049 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[Yb]>C(Cl)Cl>[CH3:14][C:12]1[S:13][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][CH3:17])=[CH:15][C:10]=2[N:11]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 23992YtterbiumHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23598944HCID 23598944, compound

Product 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 69622255(2S)-1-(2-methylbenzothiazol-5-yloxy)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[((2S)oxiran-2-yl)methoxy]-2-methylbenzothiazole, a compound of formula (3) (6.2 g, 28 mmol), and tert-butyl 1-piperazinecarboxylate, a compound of formula (4) (5.7 g, 31 mmol), in methylene chloride (200 ml), was added ytterbium (111) trifluoromethanesulfonate (1.73 g, 28 mmol). The resulting solution was allowed to stir at room temperature overnight. The solvent was evaporated (in vacuo), to yield a semi-solid, which was chromatographed on silica gel, eluting with 5% methanol/methylene chloride, to yield (2S)-1-(2-methylbenzothiazol-5-yloxy)butan-2-ol, tert butyl piperazinecarboxylate as a clear oil (9.5 g, 23 mmol).

Workup

  1. customThe solvent was evaporated (in vacuo)
  2. customto yield a semi-solid, which
  3. customwas chromatographed on silica gel
  4. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-d33019e973ea4497a1d6185fb865729b
Source dataset
uspto-grants-2006_02
Patent number
US07001909B2

Linked notes

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