Sirolimus → 1,2,3,4-Tetrahydrorapamycin

HRID 1493571Notes

Reaction equation

HRID 1493571 reaction equation
[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:64][CH3:65])[C:8]([CH3:63])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:62])[CH2:15][C@@H:16]([CH3:61])[C:17]([C@H:19]([O:59][CH3:60])[C@H:20]([OH:58])[C:21]([CH3:57])=[CH:22][C@@H:23]([CH3:56])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([OH:55])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1.C(OCC)(=O)C.CCCCCC>C1C=CC=CC=1.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:62][C@H:14]1[CH2:15][C@@H:16]([CH3:61])[C:17](=[O:18])[C@H:19]([O:59][CH3:60])[C@H:20]([OH:58])[C:21]([CH3:57])=[CH:22][C@@H:23]([CH3:56])[C:24](=[O:25])[CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]2[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([OH:55])[CH2:49][CH2:48]2)[CH3:45])[O:28][C:29](=[O:30])[C@H:31]2[N:36]([CH2:35][CH2:34][CH2:33][CH2:32]2)[C:37](=[O:38])[C:39](=[O:40])[C@:41]2([OH:43])[O:42][C@@H:5]([CH2:4][CH2:3][C@H:2]2[CH3:1])[CH2:6][C@H:7]([O:64][CH3:65])[C:8]([CH3:63])=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 5284616SirolimusHCID 21226206Ethyl acetate hexane

Product 1

HCID 1010587871,2,3,4-TetrahydrorapamycinYield 10%

Reagents, catalysts & solvents 2

HCID 178479813HCID 178479813, compoundCatalystHCID 241BenzeneSolvent

Procedure

A solution of 1 g (1.1 mmol) of rapamycin and 325 mg (351 μmol) of tris(triphenylphosphine) rhodium (I) chloride in 82 mL of benzene was hydrogenated at 50 psi for 4 days. The reaction was concentrated in vacuo affording a red foam. HPLC chromatography on a 2 inch HPLC column with 80% ethyl acetate/hexane as the eluant afforded 100 mg (10%) of 1,2,3,4-tetrahydrorapamycin as a white foam.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customaffording a red foam

Sources & evidence

ORD record
ord-bb5f3dbc40eb41c888134639bc6c5231
Source dataset
uspto-grants-1991_06
Patent number
US05023262

Reaction notes

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