Water → HCID 89514432, compound

HRID 1411105Notes

Reaction equation

O.C([O-])=O.[NH4+].C([N:13]1[C@H:19]([CH2:20][OH:21])[CH2:18][C:15]2([CH2:17][CH2:16]2)[CH2:14]1)C1C=CC=CC=1>CO.[Pd]>[CH2:16]1[C:15]2([CH2:18][C@@H:19]([CH2:20][OH:21])[NH:13][CH2:14]2)[CH2:17]1

Participants

Conditions

Temperature: 15 °C

Procedure

10% Pd/C (85 g, 4.6 wt % to the tricyclic starting material EP-019647) in a 1 L beaker was wetted with water (500 ml, 5.9 vols to Pd/C) and transferred to a N2 purged reactor. Under N2, charged MeOH (4 L) followed by ammonium formate (1.5 kg, 23.787 mol, 2.98 equiv.). The internal temperature was below 10° C. at the point. The mixture was charged more MeOH (4 L) and then heated to about 15° C. and charged a solution of above (S)-(5-benzyl-5-azaspiro[2.4]heptan-6-yl)methanol (1.78 kg) in MeOH (4 L). The resulting mixture was slowly heated to about 50° C. over the period of about 60 to 80 min. It was kept at this temperature for an additional 60 min at which point the reaction was complete as evidenced by NMR/MS/TLC. Upon cooling down, it was filtered through a pad of celite and the cake washed with DCM (8 L). The filtrate was rotavapped and chased with DCM (8 L) to afford the title compound as a yellowish thick oil. Without purification, it was used directly for the next step. ESI MS m/z (M+H)+ 128.13.

Workup

customtransferred to a N2 purged reactor
customwas below 10° C. at the point
temperatureThe resulting mixture was slowly heated to about 50° C. over the period of about 60 to 80 min
temperatureUpon cooling down
filtrationit was filtered through a pad of celite
washthe cake washed with DCM (8 L)

Sources & evidence

ORD record: ord-e4ceb9f8e1fa485eafd4aae7bd78f7dd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921573B2

Reaction notes

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