Ytterbium → tert-Butyl piperazine-1-carboxylate

HRID 1827876Notes

Reaction equation

HRID 1827876 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 210236065-(((R)-oxiran-2-yl)methoxy)-2-methylbenzo[d]thiazole

Product 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 69600520HCID 69600520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[((2R)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 (2R)-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-cf496e8b3a1f418e8229ac4f69409dc5
Source dataset
uspto-grants-2006_06
Patent number
US07056924B2

Reaction notes

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